1,4-Sorbitan is a precursor to environmentally-benign surfactants; however, sulfuric acid is currently used for the production of this compound from sorbitol (Figure 1).1,2 Solid catalysts would be favorable alternatives to the homogeneous acids, but the successive dehydration of 1,4-sorbitan to isosorbide readily happens.1 Selective synthesis of 1,4-sorbitan has remained a challenge.3 In this work, a strategy to afford high yields of 1,4-sorbitan is proposed.The dehydration of sorbitol was performed with various solid catalysts at 403 K under neat conditions (Table 1). Sulfated zirconia gave the highest yield of 1,4-sorbitan (60%) (entry 2). Zeolites and sulfonic acid resins provided less than 40% yields due to lower selectivity (entries 3-7), even under the optimized conditions (not shown). Kinetic study and adsorption experiments have revealed that sulfated zirconia preferentially adsorbs sorbitol over 1,4-sorbitan, which inhibits the successive dehydration of 1,4-sorbitan.References 1. H. Kobayashi, A. Fukuoka, Green Chem. 15 (2013) 1740.2. M. Rose, R. Palkovits, ChemSusChem 5 (2012) 167.3. Y. Morita, S. Furusato, A. Takagaki, S. Hayashi, R. Kikuchi, S. T. Oyama, ChemSusChem 7 (2014) 748.

Adsorption-controlled conversion of sorbitol to 1,4-sorbitan over sulfated zirconia

248th National Meeting (2014)

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